


Twenty Questions

by brightpinkpeppercorn



Category: Endless Summer (Visual Novel)
Genre: F/M, Oral Sex, Sex, Vaginal Sex
Language: English
Status: Completed
Published: 2020-06-17
Updated: 2020-06-17
Packaged: 2021-03-04 05:34:36
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,164
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24768598
Author URL: https://archiveofourown.org/users/brightpinkpeppercorn/pseuds/brightpinkpeppercorn
Summary: Taylor will tell Jake about her dream if he plays Twenty Questions with her
Relationships: Jake McKenzie & Main Character (Endless Summer), Jake McKenzie/Main Character (Endless Summer)
Comments: 2
Kudos: 22





	Twenty Questions

_Rhythmically, the flat of a tongue lapped at the wet folds in between her legs. She pushed her head back into the mattress of the plush bed as her back arched and her hands desperately grasped at the the cotton sheets. A pair of strong hands crawled up her spread thighs, settling on her hips, keeping her steady. Squeezing her eyes shut, she bit down on her lower lip, hard, to keep from being too loud. The tongue dragged towards her hooded, sensitive bundle of nerves, causing her to give in and moan loudly as it moved in small, slow circles._

_“Oh my God …” Releasing her grip on the sheets, her hands glided down her body until they landed in a mess of … rough, coarse, beachy hair? Curling up, she opened her eyes and her blue eyes met another pair of … blue eyes? Keeping eye contact, he retracted his tongue, replacing it with his lips as he gently started sucking. “Oh, Jake!”_

_Jake?!_

Panting, her eyes shot open and widened. The room was mostly dark, the only light filtering in under the door. Attempting to sit up, she felt the weight of a strong, muscular arm across her torso with a hand curled around her waist. The sound of gentle snoring filled the otherwise silent room at, she glanced towards the clock, 9:30 pm?

Moving his arm, she sat up in the bed, bending her knees and hugging them. Reorienting herself, she remembered how she ended up sleeping in his bed.

***  
The group had been lounging lazily after they had cleaned up from Raj’s feast celebrating their return from the La Huerta Observatory. Her feet were kicked up on a table as she watched him. His brown eyes sparkled as he tossed and caught a tennis ball while talking to his best friend, Craig. Twirling a strand of blond hair around her finger, she reminisced over that experience they shared in the observatory’s pod. 

Their bodies were pressed close together in that tight space, her nose pushed against his chest. He smelled so good, a light, crisp sent filling her senses. In an instant, the pitch dark of the pod was replaced by beautiful, majestic swaths of color; stars, constellations, and galaxies illuminated their surroundings.

Something inside her stirred, there was an innate need to be close to him. After exchanging pleasantries and small talk, him telling her how beautiful she was, she batted her eyes and got up on her toes to kiss him.

What a kiss it was. She was insatiable, needing more. As abruptly as it had started, however, it ended, much to her disappointment.

It was like when she was in the control tower with … her gaze drifted over to the Pilot. Leaning back against the bar, he took a sip of whatever whiskey was available and gave her a wink.  
Jake McKenzie was sexy as hell. Long, beach combed brown hair that fell right to the nape of his neck, large piercing blue eyes that changed shades based on his moods, ever present stubble, and that smile. She didn’t know what made her feel weaker, the smile or that smirk of his. Wait, yes she did. It was the smirk. 

Scowling, she looked away and turned her attention to the cosmopolitan that was sitting on the table in front of her. She couldn’t figure him out. He was rude and cynical. Never failed to crack some sort of wise ass comment anytime anyone had something to suggest or even say. His Navy training and “life experiences” made him believe he had the answer for everything.

Despite her better judgement, she hoped to steal another glance, her eyes darting towards him a second time. Again, his eyes met hers and he raised his glass, cocking his head to the side. His long hair was in his eyes and she made a point to push her own long, blond hair back, hoping he’d get the hint. He didn’t and just smirked at her.

Honestly, he could be soft when he wanted, especially around her. He assigned everyone a nickname but hers was the most affectionate: Princess. In general, though, he seemed to enjoy irritating everyone. There was a chip on his shoulder but what exactly was it? She knew if asked, he’d tell her. For some reason, he was an open book when it was it just the two of them.

Huffing, she tried not to let that smirk get to her. Not think about how he saved her from the plane explosion, telling her he wasn’t leaving the island without her. Not think about that climb they went on to find the observatory, when he stared at her a little too long. Not think about about when he offered to let her cuddle up with him on the way to the observatory, she turned him down and thought it best to just have Diego be her big spoon.

Forcing herself to look away, she put her feet down and took a small sip of her drink. Just then, she felt the presence of someone sitting down next to her. Smiling, she looked in his direction. Sean Gayle. The charming, handsome, kind, self-proclaimed leader of their group. Her eyes scanned him from head to toe, he really couldn’t be more opposite of Jake.

Her lips twitched into a smile as his large hand found her small one, gently squeezing it. Tilting her head towards him, she let out a deep breath and narrowed her eyes at him. Sitting there, thinking about the Pilot had put her in a mood and she may as well finish what she started with Sean. Leaning in, she suggested in a sultry voice, “Wanna go up to your room?” Eagerly, he nodded and stood up. 

Though the prospects of what to come with Sean were exciting, it was Jake watching her leave that made Taylor hitch her breath and cheeks flush.

Sean and Taylor sat down next to each other on his bed after silently walking into his room. Slowly, with some hesitation, he brought his lips to hers, kissing her. It was a nice, soft kiss but she wanted more. She wanted to feel his tongue, well any tongue, in her mouth. Quietly moaning, she ran his tongue across his lips, hoping he’d part them to invite her in. Instead, he shifted his head to the other side.

Lifting up his tshirt, her hands snaked onto his abs, relishing how hard and muscular they were. Groaning, he seemed to enjoy that and moving closer to him, she wrapped her arms around neck. Just as he helped ease her into his lap, she felt him yawn. Breaking away, Taylor raised an eyebrow at him. “Are you tired, Sean?”

Shaking his head, she gave her a sheepish smile and scratched the back of his head. “Yeah. Still wiped from that trip to the observatory.” He helped her off his lap and laid down on the bed. “Think we could take a quick nap or something? Maybe pick back up later? I definitely want to do this with you, Taylor.”

***  
Stirring awake, Sean slowly opened his eyes and saw Taylor sitting up, lost in thought. His voice was thick with sleep and he cleared his throat. “You alright, Tay?”

Turning her head and laying it on her knees, she gave him a small smile. “Yeah.” Sighing, she straightened out. “I’m sorry, Sean. I just … I don’t think things will work out between us.”

Biting the inside of his bottom lip, he slowly nodded his head. “Well. That does make me sad.” Sitting up, he put an arm around her shoulders. “I guess I did recently break up with Michelle. Thought it’d be fun to have a summer fling while we’re out here.”

Taylor would have been amenable to that relationship if they were truly out there for a week. But with no way to get off the island, who knows how long that would be. Probably best not to start things up with him. Patting his arm, she shuffled to get out of the bed. “Goodnight, Sean.” Giving him a small wave, she exited the room.

Running her hands through her hair, she shook her head to try to rid herself of that dream. God, her heart was still pounding. Somehow the pleasure she felt during the dream was still present. While making a beeline for her room, she recognized a door and abruptly stopped in front of it.

Taking a deep breath, she smoothed down her hair and blue tank top. She mumbled under her breath, “here goes nothing”, and quickly rapped on the door. All she could feel was her heart beating as each second went by excruciatingly slow.

Eventually, the door opened. There he was on the other side. Gone were the green bomber jacket, black tshirt, and jeans. Instead, he sported a white tshirt half a size too large for him and loose gray sweatpants which sat low on his slim hips. Clicking his tongue, he leaned against the door frame and crossed his arms. “You lost, Princess?”

“Yeah.” She looped her thumbs the waist of her shorts and bit her lip, feeling mischievous. “You always open the door dressed as a slut?”

Taking a second to realize what she meant, he grinned and shrugged. “I save my finest lingerie for entertaining my favorite visitors.”

Shifting her weight, she tried to peer inside his room. “You up for some company or do you already have some?”

“Just me and my good friend, Mr. Daniels.” Jake stood in place and raised an eyebrow at her. “Last I saw, you were walking off with Cap. Somethin’ happen between you two?”

“Mm, that’s really none of your business.” Pouting, she turned on her heel and waved her hand. “I guess I can go see what Diego is up to.”

Momentarily, he remained in the doorway and looked at her. Her blond hair bounced on her shoulders and her hips swayed in just the way he liked as she started walking away. He called out after her, “You want Jack Daniels or Red Stripe?”

Beaming to herself, she turned around and nonchalantly walked back towards his room. “Still have a small bottle of Moët in your room?” As she moved past him, she tossed her hair behind her hair, hoping to waft the warm smell of her shampoo towards him.

“You’re such a Princess.” Closing the door, he watched her saunter her way to the couch in his suite.

A mini bottle of champagne and a finger of whiskey later, she was draped on that couch, laughing at something he said. It probably wouldn’t have been funny if he told her the story at the feast but she was overcome with laughter. Finishing his last sip of his drink, he gave her a thoughtful look from his spot on the edge of his bed. “So … Princess. Not that I mind but what’s the real reason you’re here? Shouldn’t you still be with the hunky football player.”

“I plead the fifth.” She hoped that answer would warrant a subject change. Slowly, she stood up, gained her composure, and started picking up the empty bottles of various alcohol to throw away. Her face was hot, thinking about that dream again, and she hoped she wasn’t blushing. It didn’t help matters that he leaned back on the bed, propping himself up on his arms, watching her. Part of Taylor wanted to leave his room and forget the dream happened but another part wanted to see if real life Jake was anything like dream Jake.

Walking over to him, she put her hands on her hips. After taking a very deep breath, she blurted out, “I had a dream about you!”

“Yeah?” An amused look was on his face. “Dream or nightmare?”

Taylor plopped down on the bed next to him causing the action to bounce him up a bit. “Wouldn’t you like to know.” Biting her lower lip and smiling, she kicked her shoes off across the room.

“Yeah … yeah, I would.” Starting at her now bare feet, his eyes slowly roamed up her body until he met her eyes. “I’d like to know if you think I’m a nightmare. Personally, I like to think I’m a dream.”

Tossing her head back, she let out a laugh. “You may have a different definition of that compared to the general populace.” Moving closer to him so that their legs were touching, she tapped her chin. “I don’t know much about you, Top Gun but …” He raised his eyebrows at her, curious what she would say. “I bet I can guess something about I know about you. **I know you love to play games.** ”

Tilting his head towards her, his head barely grazing her forehead, he lowered his voice. “Depends on the game.”

“I recall you yelling at me about 20 questions.”

Groaning, he ran his hand down his face. “I hate that game, Princess.”

She walked her fingers up his arm and could feel goosebumps. “I’ll tell you about my dream if you play 20 questions with me.”

Resigning, he nodded. There was something about her blue eyes that’d make him do or say whatever she wanted. Tonight, though, sitting next to him, barely tapping him with her fingers, she had a different energy than usual. “Okay. But you ask 10 and I’ll ask 10.” Taylor reached out her hand for a handshake but Jake held onto it, running his thumb over her knuckles.

Clearing her throat, she attempted to tug her hand back but he kept a grip on it. The simple, soft touch was enough to start sending electricity throughout her body. “Jake, can I have my hand back?”

He let go of her hand. “Nine more questions, Princess.” Mouth agape, she tried to protest but he put a finger to her lips. “Just playing by the rules.”

Gripping his wrist, Taylor gave that finger a gentle kiss before running her tongue over the length and kissing the top of his finger. “You like that?”

“Eight. And yeah, I did.”

“Hmm” She got up on her knees and faced him, noticing his brown hair had fallen again in front of his yes. “By the way, when I pushed my hair back earlier, it was because I was trying to tell you your hair was in your face.”

He chuckled. “You need to phrase that in the form of a question.”

Rolling her eyes, she cupped his face in one hand and combed back his hair with the other. His eyes closed and he let out an audible breath. “Do you like that, Jake?” Nodding he flashed her five fingers followed by two. Keeping her fingers moving, she leaned towards his ear, letting her warm breath tickle his ear. She whispered, “You ever dream about me?”

Opening his eyes, he turned his head, his lips barely brushing against hers. “Maybe. You got six questions left.”

Slowly, she licked her bottom lip. Their faces were dangerously close and she fought all urges to kiss him at that moment. “When you watched me leave with Sean, were you jealous?”

“You bet your ass I was.” His eyes darted down to her lips and then back up to her eyes. “Five.”

Taylor took a deep breath and sat back. Her heart was racing and her face was probably even more red than before. She needed something to cool down. At least until after their game was over. Maybe then she could start working on that dream. “D-do you like puppies and kittens?”

“Huh.” His eyes widened slightly, taken aback. “Yeah, I like puppies and kittens. Dogs and cats. Make those last three questions count, Princess.”

She fanned herself slowly with her hand and crossed her arms looking at him. Her voice came out shaky and she took a deep breath. Cool down time was over and Jake, in the gray sweats and white tshirt, hair hanging down as his head was slightly tilted back, looking at her, never looked more desirable. “Jake … do you like me?”

“Depends on what you mean by the question.” He winked at her and she furrowed her eyebrows at his vague statement. “Yes, I like you.” Anticipating when he’d say next, she joined him in saying, “Two more.”

Her hand moved onto his leg and her fingernails slightly grazed his inner thigh over the gray fabric, eliciting a low hum from him. “You wear boxers?”

“Find out for yourself, Princess.” Getting down on her hands and knees, she dragged her nails up his leg. He groaned when they ran over his stiffening member. Upon reaching his waistband, she slipped her fingers in, anticipating another waistband but finding nothing. She wasn’t surprised, she’d been eyeing those sweatpants from the moment he opened the door.

“Oh, you naughty boy, you.”

She smirked at her, “I am to please.” His voice was low and thick and his eyes darted down to her hand, drawing small circles on the skin under his waistband. “One more question.”

“Do you want to ask me about my dream now?” Moving her hand out from under his sweatpants, she moved into a seated position.

He grinned at her. “Okay. First question.” Scooting over to the edge of the bed, Jake took her hand, urging her to sit next to him. “Will you tell me if anything makes you uncomfortable?” Taylor nodded in agreement.

“Alright.” Reaching over, he cupped her chin, drawing her face to his. “In your dreams, did this happen?” Gently, he pressed his lips against hers and waited a moment before taking her lower lip in between his. She returned the kiss, softly at first before tilting her head to the side, deepening it and increasing the urgency. Parting her lips with his tongue, he entered her mouth and stroked her tongue with his. It was exactly the kiss she had been craving earlier.

Letting out a soft moan, Taylor pulled away and gave him a last, quick kiss. “Uh. Wow. Um … no. That’s not what happened.” She wiped her mouth with the back of her hand before announcing that he was on question three.

“Hmm … What about this?” Grasping her hair, he pushed it off of her neck and behind her shoulder before moving her head back, exposing her neck. Wetting his lips, he alternated slow, open mouth kisses with small pecks on her skin, trailing from her collar bone all the way up to her jaw.

Her breaths were shallow and her eyes closed. “N-no. This didn’t happen.”

Jake sat back and scratched his chin, scanning her body. His eyes locked with hers and he lowered his voice again. “Okay. Question five. Can you take your clothes off? Leave your panties on.”

“Yes.” Without hesitation, she stood up and slowly peeled off her tank top. Pausing, she let him admire her. Unbuttoning her shorts, she let them fall to the floor before stepping out of them. Finally, her hands reached around for the clasp of her bra and unhooked it, allowing it to fall off her and drop to the floor. Leaning back, he drank her in and let out a long, low whistle. Jake crooked his finger towards him. She took her head. “Nuh uh. You have to ask me.”

“Question six. Will you sit in my lap, Princess?” Placing her hands on his shoulders, she climbed into his lap and let her legs rest on either side of his waist. “Question seven: was this in your dream?” Placing his hands on her back, he drew her in and pushed his face into her chest. Looking up, he noticed her lick her upper lip in anticipation. Dragging his mouth across her skin, he kissed one of her breasts before flicking her nipple with his tongue. Arching her head back, she let out a content sigh. A hand moved to roughly massage her other breast and gently pinched her nipple. That warm sensation she felt in her lower abdomen when she woke up had returned and was growing, moving down her body, dampening the area in between her legs.

Gently, he continued to suck on her nipple and she moaned again. “Uh, Jake … this wasn’t in my dream, either.”

Letting go, he rested his head against her chest again, taking a deep breath. “Question eight.” Pulling back, he glanced up at her. “Can you lay on your back?”

Slipping off of him, she fell back and landed on her back, looking up at him. Well, it was happening. With two questions left. Taking a hold of her legs, he pulled her to the edge of the bed and kneeled in front of her. “If your dream was anything like mine, I have a feeling I’m going to win on this round.” He took a hold of her wet panties, starting to slip them off.

“That didn’t sound like a question to me, Jacob.” Reaching down, she pulled her underwear back up.

“Princess,” he ran his hands up her thighs, settling on her hips. “Question nine: can I take your your panties off?” She signaled a yes and he yanked her last piece of clothing off. Spreading her legs, he settled himself in between them. “Question ten. Will you say my name if this was in your dream?”

“Uh uh.” Closing her eyes, she draped an arm over her eyes and sighed, loudly, as he slowly kissed her inner thigh, making sure to drag his chin to tickle her with his stubble. She hissed when she felt his fingers spread her folds and his tongue make contact with her already wet area. It was exactly her dream, her head pushed back against the mattress as he slowly lapped her up, eliciting moans from her. Nestling his face into her, he moved his fingers to stroke her while his tongue found her clit, swirling and sucking. “Oh, God.” Finding his hair, she tugged on it, hard. Her breathing was shaky and shallow and pressure was building, so close to a release. “Jake! I’m so –”

Pulling away and crouching back down on his knees, he wiped his face with his tshirt. “I win.”

Narrowing her eyes, she propped herself up on her elbows and looked at him. Taylor was wound tight for the second time that night and would finish herself off right there if she had to. “Bonus question!” He gestured for her to go on. “Jake, will you please just fuck me already?”

“Thought you’d never ask.” Quickly, he shed his two articles of clothing and helped her move onto back onto the bed before climbing over her. Looking down at her, their blue eyes met as they gave each other a small smile. Leaning down, he kissed her as she moved her legs apart, allowing him to enter her.

There was a small gasp from Taylor as she took a moment to accommodate him. Throwing her arms around his neck, she continued to kiss him as they rocked together, slowly at first. One of his hands focused again on her clit, moving in small circles and pinching. She moaned, loudly, into his mouth as he continued thrusting and working her bundle of nerves.

Breaking their kiss, she arched her head back and closed her eyes, finally feeling ripples of pleasure throughout her body as she finally went over the edge. “Oh, Jake!” He moved his hands to either side of her and thrust several more times before hitting his own release.

Rolling on his back next to her, they worked to catch their breaths. Picking up his tshirt again, he wiped the perspiration off her forehead before doing the same to his own. “So, Taylor …”

“Taylor?”

“Not feeling annoyed right now.” He wiped down his chest with the tshirt. “Anyway. Bonus question, how was that compared to your dream?”

She turned her head to look at him. “I couldn’t even dream of something like that.”

“Maybe you chose the wrong guy to walk off with.”

Taylor raised an eyebrow. “Sean? I’m not …” She smiled wide at him, “You are jealous!” He shrugged and she shook her head. “Well, maybe I should get back to my room and get some sleep.” Sitting up, she adjusted to climb out of his bed.

Before she could, he took a hold of her wrist. “Stay with me tonight, Princess?” The request was unexpected. Welcome, but unexpected. As she contemplated his request, she looked back down at him. His hair was tousled, his eyes were a darker shade of blue, and he was smirking at her. This was the side of him he reserved just for her and she couldn’t help but give in.

“Maybe just tonight.”

Laying back down, she rolled onto her side. He joined her, spooning her from behind as he pulled a blanket over then. Giving her temple a kiss, he mumbled, “Goodnight, Princess.” he kissed her temple again and whispered, “Sweet dreams.”


End file.
